SIMONTON COURT HISTORIC INN & COTTAGES, Key West

Simonton Court Historic Inn & Cottages - An adults-only oasis with four pools, historic cottages, and tropical gardens in Old Town

Set on two meticulously landscaped acres in Old Town, this Key West hotel features four shimmering pools surrounded by flowering vines and palm fronds. The property encompasses restored Victorian and Conch architecture, including 1880s cigar workers' cottages and a historic mansion. Simonton Court Historic Inn & Cottages offers 30 unique rooms across five buildings, with accommodations ranging from petite queens to two-story cottages with lofts. The cottages showcase exposed Dade County pine, wood floors, and private porches with swings and rocking chairs. Guest rooms include air conditioning, minibars, and tea/coffee facilities, while some units feature pool views or direct pool access. A complimentary continental breakfast is served daily, and the property maintains an honor bar. Located just off Duval Street, Simonton Court places guests within 0.5 miles of Mallory Square, Key West Aquarium, and the Truman Little White House.

Pros

Four 24-hour swimming pools accessible to all guests

Private porches with swings and rocking chairs in cottage accommodations

Complimentary welcome drinks and daily continental breakfast

Secluded tropical gardens with brick pathways

Cons

Adults-only policy excludes families with children under 18

Limited on-site dining options beyond breakfast service